1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene → 5-[2',3-Difluoro-4'-(trifluoromethoxy)biphenyl-4-yl]pyrazin-2-amine

HRID 1523969Notes

Reaction equation

HRID 1523969 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.[F:24][C:25]1[CH:30]=[C:29]([O:31][C:32]([F:35])([F:34])[F:33])[CH:28]=[CH:27][C:26]=1Br>>[F:24][C:25]1[CH:30]=[C:29]([O:31][C:32]([F:33])([F:34])[F:35])[CH:28]=[CH:27][C:26]=1[C:6]1[CH:5]=[CH:4][C:3]([C:17]2[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=2)=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 220652111-Bromo-2-fluoro-4-(trifluoromethoxy)benzeneHCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine

Product 1

HCID 903135565-[2',3-Difluoro-4'-(trifluoromethoxy)biphenyl-4-yl]pyrazin-2-amine

Procedure

The title compound was prepared using analogous conditions to those described in Example 1 utilizing 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazin-2-amine and 2-fluoro-4-(trifluoromethoxy)bromobenzene. MS (ESI): mass calcd. for C17H10F5N3O, 367.07; m/z found, 368.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (s, 1H), 8.03-7.96 (m, 2H), 7.78 (m, 1H), 7.56-7.49 (m, 3H), 7.37 (d, J=8.2, 1H), 6.75 (s, 2H).

Sources & evidence

ORD record
ord-d97d98de0ece49028dd61762b9c81bf0
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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